[2-[(2S)-2-propan-2-ylaziridine-1-carbonyl]phenyl]methyl benzoate | 1430334-90-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [2-[(2S)-2-propan-2-ylaziridine-1-carbonyl]phenyl]methyl benzoate
• CAS: 1430334-90-9
• 化学式: C₂₀H₂₁NO₃
• 分子量: 323.392
• InChiKey: FQSMPAHVLYTLEV-ITUIMRKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  46.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [2-[(2S)-2-propan-2-ylaziridine-1-carbonyl]phenyl]methyl benzoate 在 三乙氧基硅烷 、 zinc diacetate 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  Aziridine ring-containing chiral ligands as highly efficient catalysts in asymmetric synthesis

  摘要：

  Enantiomerically pure bidentate heteroorganic ligands built on an achiral skeleton containing hydroxyl and aziridine moieties as nucleophilic centers, capable of binding various organometallic reagents, have proven to be highly efficient catalysts in the enantioselective addition of diethylzinc and phenylethynylzinc to aryl and alkyl aldehydes to give the desired chiral products in high chemical yields (up to 90%) and with ees of up to 95%. The influence of the stereogenic center located in the carbon atom in the aziridine moiety on the stereochemical course of the reaction is reported. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.03.001
• 作为产物：
  描述：

  2-苯甲酰氧基甲基苯甲酸 在 吡啶 、 氯化亚砜 、 三乙胺 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 0.83h， 生成 [2-[(2S)-2-propan-2-ylaziridine-1-carbonyl]phenyl]methyl benzoate
  参考文献：
  名称：

  Aziridine ring-containing chiral ligands as highly efficient catalysts in asymmetric synthesis

  摘要：

  Enantiomerically pure bidentate heteroorganic ligands built on an achiral skeleton containing hydroxyl and aziridine moieties as nucleophilic centers, capable of binding various organometallic reagents, have proven to be highly efficient catalysts in the enantioselective addition of diethylzinc and phenylethynylzinc to aryl and alkyl aldehydes to give the desired chiral products in high chemical yields (up to 90%) and with ees of up to 95%. The influence of the stereogenic center located in the carbon atom in the aziridine moiety on the stereochemical course of the reaction is reported. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.03.001

文献信息

• Aziridine ring-containing chiral ligands as highly efficient catalysts in asymmetric synthesis
  作者：Michał Rachwalski、Szymon Jarzyński、Stanisław Leśniak

  DOI：10.1016/j.tetasy.2013.03.001

  日期：2013.4

  Enantiomerically pure bidentate heteroorganic ligands built on an achiral skeleton containing hydroxyl and aziridine moieties as nucleophilic centers, capable of binding various organometallic reagents, have proven to be highly efficient catalysts in the enantioselective addition of diethylzinc and phenylethynylzinc to aryl and alkyl aldehydes to give the desired chiral products in high chemical yields (up to 90%) and with ees of up to 95%. The influence of the stereogenic center located in the carbon atom in the aziridine moiety on the stereochemical course of the reaction is reported. (c) 2013 Elsevier Ltd. All rights reserved.